The goal of this program is to develop new strategies for the synthesis of bioactive molecules in the prenylated indole alkaloid family. The complex natural products that we construct, and their unique derivatives which are only accessible using our strategies, will provide small molecules that will serve as a starting point to identify anticancer compounds that function via novel mechanisms. Our synthetic studies should also lead to insights into the biosynthesis of a subset of the prenylated indole alkaloids for which the biogenesis is not established. Specifically, we intend to develop strategies to synthesize different structural classes of prenylated indole alkaloids including the citrinalins, cyclopiamine, citrinadins and the stephacidins.